Synthesis of a Tetranuclear Organooxotin Cage by Debenzylation Reactions:  X-ray Crystal Structure of [(PhCH2)2Sn2O(O2P(OH)-t-Bu)4]2

Chandrasekhar, Vadapalli; Baskar, Viswanathan; Steiner, Alexander; Zacchini, Stefano

doi:10.1021/om020531r

Cited by 66 publications

(50 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The average SnÀO bond length for the nearly planar distannoxane core is 2.114(1) , which is comparable with literature reports (2.125 ). [22][23][24] Compounds 7 and 8 are ladder framework stannoxanes (Sn 4 O 4 ) supported by a central Sn 2 O 2 distannoxane ring.…”

Section: Resultsmentioning

confidence: 99%

Inorganic‐Cored Photoactive Assemblies: Synthesis, Structure, and Photochemical Investigations on Stannoxane‐Supported Multifluorene Compounds

Chandrasekhar¹,

Thilagar²,

Steiner³

et al. 2006

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Organostannoxanes were used as inert supports for the preparation of multichromophore assemblies. The synthesis involves a single-step procedure and allows the preparation of compounds in which the number of chromophore units can be varied from one to six. Thus, the reactions of LCOOH (1-fluorenecarboxylic acid) or L'COOH (9-fluorenecarboxylic acid) with various organostannoxane precursors afforded the fluorenyl derivatives [Ph(3)SnO(2)CL] (1), [Ph(3)SnO(2)CL'] (2), [{nBu(3)SnO(2)CL''}(n)] (3), [{nBu(3)SnO(2)CL'}(n)] (4), [{tBu(2)Sn(OH)O(2)CL}(2)] (5), [{tBu(2)Sn(OH)O(2)CL'}(2)] (6), [{[nBu(2)SnO(2)CL](2)O}(2)] (7) [{[nBu(2)SnO(2)CL'](2)O}(2)] (8), [{nBuSn(O)O(2)CL}(6)] (9), and [{nBuSn(O)O(2)CL'}(6)] (10). Interestingly, the formation of 3 is accompanied by an unusual oxo-transfer reaction. The ligand L is oxidized at the 9-position. Compounds 1, 3, 5, 7, and 8 were characterized by X-ray crystallography. The solid-state structures of these compounds reveal rich supramolecular structures owing to multiple intermolecular interactions between the various supramolecular synthons present in these molecules. The optical behavior of 1-10 is primarily dictated by the fluorenyl periphery. These compounds display strong blue fluorescent emission in solution and blue-green fluorescent emission in the solid state. Fluorescence lifetimes of all of these compounds are on the nanosecond timescale, and this suggests that the emission originates from the singlet excited state to the ground state. Intermolecular interactions in the solid state lead to considerable broadening of the emission bands.

show abstract

Section: Resultsmentioning

confidence: 99%

Inorganic‐Cored Photoactive Assemblies: Synthesis, Structure, and Photochemical Investigations on Stannoxane‐Supported Multifluorene Compounds

Chandrasekhar¹,

Thilagar²,

Steiner³

et al. 2006

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

show abstract

“…Such dimerization of intermediates to eventual products has been reported by our group recently. [15] The two tin atoms in 4 are bridged by two hydroxyl groups (O1 and O1*) to generate a central Sn 2 O 2 stannoxane core. Each tin atom is bound to one ferrocene carboxylate and only one oxygen atom (O2) of the ferrocene carboxylate is bound to the tin atom.…”

Section: Resultsmentioning

confidence: 99%

Organostannoxane‐Supported Multiferrocenyl Assemblies: Synthesis, Novel Supramolecular Structures, and Electrochemistry

Chandrasekhar

Gopal

Nagendran

et al. 2005

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Organostannoxane-based multiredox assemblies containing ferrocenyl peripheries have been readily synthesized by a simple one-pot synthesis, either by a solution method or by room-temperature solid-state synthesis, in nearly quantitative yields. The number of ferrocenyl units in the multiredox assembly is readily varied by stoichiometric control as well as by the choice of the organotin precursors. Thus, the reaction of the diorganotin oxides, R2SnO (R = Ph, nBu and tBu) with ferrocene carboxylic acid affords tetra-, di-, and mononuclear derivatives [{Ph2Sn[OC(O)Fc]2}2] (1), [{[nBu2SnOC(O)Fc]2O}2] (2), [nBu2Sn{OC(O)Fc}2] (3), [{tBu2Sn(OH)OC(O)Fc}2] (4), and [tBu2Sn{OC(O)Fc}2] (5) (Fc = eta(5)C5H4-Fe-eta(5)C5H5). The reaction of triorganotin oxides, R3SnOSnR3 (R = nBu and Ph) with ferrocene carboxylic acid leads to the formation of the mono-nuclear derivatives [Ph3SnOC(O)Fc] (6) and [{nBu3SnOC(O)Fc}(n)] (7). Molecular structures of the compounds 1-4 and 6 have been determined by single-crystal X-ray analysis. The molecular structure of compound 1 is new among organotin carboxylates. In this compound, ferrocenyl carboxylates are involved in both chelating and bridging coordination modes to the tin atoms to form an eight-membered cyclic structure. In all of these compounds, the acidic protons of the cyclopentadienyl groups are hydrogen bonded to the carboxylate oxygens (C-HO) to form rich supramolecular assemblies. In addition to this, pi-pi, T-shaped, L-shaped, and side-to-face stacking interactions involving ferrocenyl groups also occur. Compound 6 shows an interesting and novel intermolecular CO2-pi stacking interaction. Electrochemical analysis of the compounds 1-4, 6, and 7 shows a single, quasi-reversible oxidation peak corresponding to the simultaneous oxidation of four, two, and one ferrocenyl substituents, respectively. Compound 5 shows two quasi-reversible oxidation peaks. This is attributed to the positional difference among the ferrocenyl substituents on the tin atom. Additionally, while compounds 2 and 4 are electrochemically quite robust and do not decompose even after ten continuous CV cycles, compounds 1, and 3, 5-7 start to show decomposition after five cycles.

show abstract

“…In the crystal lattice, the cations 6a are associated with the triflate anions through O(4)-H(4)···O (6) and O(5)-H(5)···O(7a) hydrogen bonds giving rise to the formation of an infinite chain (symmetry operation: a ϭ Ϫx, y Ϫ1/2, Ϫ1/ 2 Ϫ z), as shown in Figure 2. The O(4)···O (6) and O(5)···O(7a) distance of 2.789(6) and 2.791(6) Å , respectively, and the position of the corresponding OH stretching vibration ν(OH) at 3338 cm Ϫ1 in the IR spectrum of 6 are indicative of medium-strength hydrogen bonding.…”

Section: Wwweurjicorgmentioning

confidence: 99%

The Isoelectronic Replacement of E = P⁺ and Si in the Trinuclear Organotin−Oxo Clusters [Ph₂E(OSntBu₂)₂O·tBu₂Sn(OH)₂]

et al. 2003

View full text Add to dashboard Cite

show abstract

Synthesis of a Tetranuclear Organooxotin Cage by Debenzylation Reactions: X-ray Crystal Structure of [(PhCH₂)₂Sn₂O(O₂P(OH)-t-Bu)₄]₂

Cited by 66 publications

References 17 publications

Inorganic‐Cored Photoactive Assemblies: Synthesis, Structure, and Photochemical Investigations on Stannoxane‐Supported Multifluorene Compounds

Inorganic‐Cored Photoactive Assemblies: Synthesis, Structure, and Photochemical Investigations on Stannoxane‐Supported Multifluorene Compounds

Organostannoxane‐Supported Multiferrocenyl Assemblies: Synthesis, Novel Supramolecular Structures, and Electrochemistry

The Isoelectronic Replacement of E = P⁺ and Si in the Trinuclear Organotin−Oxo Clusters [Ph₂E(OSntBu₂)₂O·tBu₂Sn(OH)₂]

Contact Info

Product

Resources

About

Synthesis of a Tetranuclear Organooxotin Cage by Debenzylation Reactions: X-ray Crystal Structure of [(PhCH2)2Sn2O(O2P(OH)-t-Bu)4]2

Cited by 66 publications

References 17 publications

Inorganic‐Cored Photoactive Assemblies: Synthesis, Structure, and Photochemical Investigations on Stannoxane‐Supported Multifluorene Compounds

Inorganic‐Cored Photoactive Assemblies: Synthesis, Structure, and Photochemical Investigations on Stannoxane‐Supported Multifluorene Compounds

Organostannoxane‐Supported Multiferrocenyl Assemblies: Synthesis, Novel Supramolecular Structures, and Electrochemistry

The Isoelectronic Replacement of E = P+ and Si in the Trinuclear Organotin−Oxo Clusters [Ph2E(OSntBu2)2O·tBu2Sn(OH)2]

Contact Info

Product

Resources

About

Synthesis of a Tetranuclear Organooxotin Cage by Debenzylation Reactions: X-ray Crystal Structure of [(PhCH₂)₂Sn₂O(O₂P(OH)-t-Bu)₄]₂

The Isoelectronic Replacement of E = P⁺ and Si in the Trinuclear Organotin−Oxo Clusters [Ph₂E(OSntBu₂)₂O·tBu₂Sn(OH)₂]